Let’s start at #16 with an incredibly heartbreaking moment from the 2011 Preakness. Why was it heartbreaking? Because your’s truly had the boxed exacta of Shackleford and Astrology with a boatload riding on it. How much is a boatload? Try $5,700 worth of cold, hard cash if those two just wind up 1-2 in either order.

Wanna see how close ol’ Drewski was to $5,700? Watch below and weep along with me as those two horses pull away from the field in the last 500 yards, only to see that scumbag Animal Kingdom come out of nowhere to steal $5,700 from me.